A general synthetic route of dihydroagarofuran sesquiterpenoid from α- (-)-santonin

Article abstract of DOI:10.1016/S0040-4039(98)01766-3

A general and efficient approach for synthesis of dihydroagarofuran sesquiterpenoid, the core structure of the polyol esters extensively present in the Celastraceae plants, has been developed by a series of transformations, which mainly include three creative and synthetically valuable conversions: the strategic double-bond shifting of 3, the versatile rearrangement of epoxide 5 generating two key functions, the C5-OH and 7,11- Double-bond, and the stereoselective cyclization/reduction of 8 constructing the tetrahydrofuran ring of 11. Thus the sesquiterpenoid 3α,6α, 12- trihydroxy-dihydoagarofuran 1 was synthesized.